Visible-Light-Mediated Direct Amidation of Arenes and Heteroarenes with N-Aminopyridinium Salts

被引:3
作者
Xia, Cencen [1 ]
Hao, Xinyu [1 ]
Jin, Kun [1 ]
Zhang, Rong [1 ]
Duan, Chunying [1 ]
Li, Yaming [1 ]
机构
[1] Dalian Univ Technol, Sch Chem Engn, State Key Lab Fine Chem, Dalian 116024, Liaoning, Peoples R China
基金
中国国家自然科学基金;
关键词
photocatalysis; amidopyridinium salts; amidation; 3+2]-annulation; radical reactions; AMIDE BOND FORMATION; C-H AMIDATION; COUPLING REAGENTS; AMINOHYDROXYLATION; FUNCTIONALIZATION; INHIBITION; ALDEHYDES; OLEFINS; AMINES; CELL;
D O I
10.1055/a-1867-7228
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel photoinduced strategy has been developed for the C-H amidation of aromatics and heteroaromatics by using benzamide radicals with free NH groups generated from N-amidopyridinium salts under visible-light irradiation. The new mode of activation of N-amidopyridinium salts proceeds efficiently under mild conditions to give various benzamide derivatives with free NH groups. In addition, oxazoline analogues, synthesized by the reaction with styrene, demonstrate a substantial range of prospective applications for this versatile protocol.
引用
收藏
页码:1551 / 1555
页数:5
相关论文
共 53 条
[1]   Metal-catalysed approaches to amide bond formation [J].
Allen, C. Liana ;
Williams, Jonathan M. J. .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3405-3415
[2]  
Bode JW, 2006, CURR OPIN DRUG DISC, V9, P765
[3]   Understanding the structure/reactivity of aminium/uronium salts as coupling reagents in peptide synthesis [J].
Bofill, JM ;
Albericio, F .
TETRAHEDRON LETTERS, 1999, 40 (13) :2641-2644
[4]   Visible light C-H amidation of heteroarenes with benzoyl azides [J].
Brachet, E. ;
Ghosh, T. ;
Ghosh, I. ;
Koenig, B. .
CHEMICAL SCIENCE, 2015, 6 (02) :987-992
[5]  
Butler LM, 2001, CLIN CANCER RES, V7, P962
[6]   Visible-Light Photocatalytic Functionalization of Isocyanides for the Synthesis of Secondary Amides and Ketene Aminals [J].
Cannalire, Rolando ;
Amato, Jussara ;
Summa, Vincenzo ;
Novellino, Ettore ;
Tron, Gian Cesare ;
Giustiniano, Mariateresa .
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (21) :14077-14086
[7]  
Cupido T, 2007, CURR OPIN DRUG DISC, V10, P768
[8]   Specific Btk inhibition suppresses B cell- and myeloid cell-mediated arthritis [J].
Di Paolo, Julie A. ;
Huang, Tao ;
Balazs, Mercedesz ;
Barbosa, James ;
Barck, Kai H. ;
Bravo, Brandon J. ;
Carano, Richard A. D. ;
Darrow, James ;
Davies, Douglas R. ;
DeForge, Laura E. ;
Diehl, Lauri ;
Ferrando, Ronald ;
Gallion, Steven L. ;
Giannetti, Anthony M. ;
Gribling, Peter ;
Hurez, Vincent ;
Hymowitz, Sarah G. ;
Jones, Randall ;
Kropf, Jeffrey E. ;
Lee, Wyne P. ;
Maciejewski, Patricia M. ;
Mitchell, Scott A. ;
Rong, Hong ;
Staker, Bart L. ;
Whitney, J. Andrew ;
Yeh, Sherry ;
Young, Wendy B. ;
Yu, Christine ;
Zhang, Juan ;
Reif, Karin ;
Currie, Kevin S. .
NATURE CHEMICAL BIOLOGY, 2011, 7 (01) :41-50
[9]   Large-Scale Applications of Amide Coupling Reagents for the Synthesis of Pharmaceuticals [J].
Dunetz, Joshua R. ;
Magano, Javier ;
Weisenburger, Gerald A. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2016, 20 (02) :140-177
[10]   Arylglyoxals in Synthesis of Heterocyclic Compounds [J].
Eftekhari-Sis, Bagher ;
Zirak, Maryam ;
Akbari, Ali .
CHEMICAL REVIEWS, 2013, 113 (05) :2958-3043